Stable 5-Substituted Cyclopentadienes for the Diels-Alder Cycloaddition and their Application to the Synthesis of Palau'amine

被引：56

作者：

Hudon, Jonathan ^{[1
]}

Cernak, Timothy A. ^{[1
]}

Ashenhurst, James A. ^{[1
]}

Gleason, James L. ^{[1
]}

机构：

[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2008年 / 47卷 / 46期

基金：

加拿大自然科学与工程研究理事会;

关键词：

cycloaddition; Diels-Alder reaction sigmatropic shift; synthetic methods;

D O I：

10.1002/anie.200803344

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

(Chemical Equation Presented) Putting the brakes on a hydride shift: The incorporation of a 2-silyloxy group increases both the stability and reactivity of 5-substituted cyclopentadienes, thus facilitating their preparation and use (see scheme; Bz=benzyl, TBS=tert-butyldimethylsilyl). This approach has been applied to the synthesis of the E ring in the marine alkaloid palau'amine. © 2008 Wiley-VCH Verlag GmbH & Co. KGaA.

引用

页码：8885 / 8888

页数：4

共 50 条

[1] P-225,917 synthetic studies: unusual hydroboration regioselectivity influenced by remote functional groups [J].

Ashenhurst, James A. ;

Gleason, James L. .

TETRAHEDRON LETTERS, 2008, 49 (03) :504-507

[2] THE INFLUENCE OF SIDECHAIN SUBSTITUENTS IN THE INTRAMOLECULAR DIELS-ALDER REACTION [J].

ATTAHPOKU, SK ;

GALLACHER, G ;

NG, AS ;

TAYLOR, LEB ;

ALWARD, SJ ;

FALLIS, AG .

TETRAHEDRON LETTERS, 1983, 24 (07) :677-680

[3] MODIFIED PRINS REACTION APPLICABLE TO CONJUGATED DIENES [J].

BAJOREK, JJS ;

BATTAGLI.R ;

PRATT, G ;

SUTHERLA.JK .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1974, (11) :1243-1245

[4] SYNTHESIS OF (E)-CYCLOPROPYL-3-CHLOROALANINE AND (Z)-CYCLOPROPYL-3-CHLOROALANINE [J].

BLAND, JM ;

STAMMER, CH ;

VARUGHESE, KI .

JOURNAL OF ORGANIC CHEMISTRY, 1984, 49 (09) :1634-1636

[5] Oxoammonium salts. 6. 4-acetylamino-2,2,6,6-tetramethylpiperidine-1-oxoammonium perchlorate: A stable and convenient reagent for the oxidation of alcohols. Silica gel catalysis [J].

Bobbitt, JM .

JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (25) :9367-9374

[6]

Bobbitt JM, 1999, CHEM ENG NEWS, V77, P6

[7]

BRESLOW R, 1973, TETRAHEDRON LETT, P3723

[8] ACETOXYFULVENE SYNTHESIS OF PROSTAGLANDINS - ALTERNATIVE SYNTHESIS OF COREY ALDEHYDE [J].

BROWN, ED ;

CLARKSON, R ;

LEENEY, TJ ;

ROBINSON, GE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1974, (16) :642-642

[9] Revised structure of palau'amine [J].

Buchanan, Malcolm S. ;

Carroll, Anthony R. ;

Quinn, Ronald J. .

TETRAHEDRON LETTERS, 2007, 48 (26) :4573-4574

[10] Natural products, stylissadines A and B, specific antagonists of the P2X7 receptor, an important inflammatory Target [J].

Buchanan, Malcolm S. ;

Carroll, Anthony R. ;

Addepalli, Rama ;

Avery, Vicky M. ;

Hooper, John N. A. ;

Quinn, Ronald J. .

JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (07) :2309-2317

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